Epicriptine

Epicriptine
Clinical data
Other names	beta-Dihydroergocryptine
Pregnancy; category	Contraindicated;
Routes of; administration	Oral
ATC code	N04BC03 (WHO) (alpha/beta);
Legal status
Legal status	In general: ℞ (Prescription only);
Identifiers
	IUPAC name (2R,4R,7R)-N- [(1S,2S,4R,7S)- 2-hydroxy- 7-(S)-(1-methylpropyl)- 5,8-dioxo- 4-(propan-2-yl)- 3-oxa- 6,9-diazatricyclo [7.3.0.02,6]dodecan-4-yl]- 6-methyl- 6,11-diazatetracyclo [7.6.1.02,7.012,16] hexadeca- 1(16),9,12,14-tetraene- 4-carboxamide;
CAS Number	88660-47-3;
PubChem CID	3084313;
ChemSpider	2341400;
UNII	5M64643B5U;
ChEBI	CHEBI:59925;
ChEMBL	ChEMBL1378681;
CompTox Dashboard (EPA)	DTXSID90941216 ;
ECHA InfoCard	100.039.157
Chemical and physical data
Formula	C32H43N5O5
Molar mass	577.726 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CCC(C)[C@H]1C(=O)N2CCC[C@H]2[C@]3(N1C(=O)[C@](O3)(C(C)C)NC(=O)[C@@H]4C[C@H]5[C@@H](CC6=CNC7=CC=CC5=C67)N(C4)C)O;
	InChI InChI=1S/C32H43N5O5/c1-6-18(4)27-29(39)36-12-8-11-25(36)32(41)37(27)30(40)31(42-32,17(2)3)34-28(38)20-13-22-21-9-7-10-23-26(21)19(15-33-23)14-24(22)35(5)16-20/h7,9-10,15,17-18,20,22,24-25,27,33,41H,6,8,11-14,16H2,1-5H3,(H,34,38)/t18?,20-,22-,24-,25+,27+,31-,32+/m1/s1; Key:SBFXHXZNBNFPHV-CROXOCCCSA-N;

Epicriptine or beta-dihydroergocryptine is a dopamine agonist of the ergoline class. It constitutes one third of the mixture known as dihydroergocryptine, the other two thirds consisting of alpha-dihydroergocryptine. The alpha differs from the beta form only in the position of a single methyl group, which is a consequence of the biosynthesis in which the proteinogenic amino acid isoleucine is replaced by leucine.^[1]

References

^ Steinhilber D, Schubert-Zsilavecz M, Roth HJ (2005). Medizinische Chemie (in German). Stuttgart: Deutscher Apotheker Verlag. p. 142. ISBN 3-7692-3483-9.

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[1] Steinhilber D, Schubert-Zsilavecz M, Roth HJ (2005). Medizinische Chemie (in German). Stuttgart: Deutscher Apotheker Verlag. p. 142. ISBN 3-7692-3483-9.

[1]

v t e Ergolines
Lysergic acid derivatives	2-Bromo-LSD (BOL-148) Amesergide Bromerguride (2-bromolisuride) Bromocriptine Cabergoline Dihydroergocornine Dihydroergocristine Dihydroergocryptine Dihydroergometrine (Dihydroergonovine, Dihydroergobasine) Dihydroergosine Dihydroergotamine Epicriptine Ergine (LSA; LA-111; Lysergamide) Ergocornine Ergocristine Ergocryptine Ergoloid (Dihydroergotoxine) Ergometrine (Ergonovine, Ergobasine) Ergometrinine Ergostine Ergotamine Ergotoxine Ergovaline Fludihydroergotamine Lisuride LY-215,840 LSH Lysergic acid Lysergic acid methyl ester Lysergine Lysergol Mergocriptine Mesulergine Metergoline Metergotamine MIPLA Methysergide Propisergide Sergolexole
Psychedelic lysergamides	1B-LSD 1cP-LSD 1P-ETH-LAD 1P-LSD AL-LAD ALD-52 BU-LAD CYP-LAD Diallyllysergamide (DAL) Dimethyllysergamide (DAM-57) ECPLA Ergonovine ETFELA ETH-LAD IP-LAD LAMPA LAE-32 LSD (lysergide) LPD-824 LSM-775 LSH LSD-Pip Lysergic Acid 2-Butylamide Lysergic Acid 2,4-Dimethylazetidide Lysergic Acid 3-Pentylamide Lysergic acid cyclobutylamide Lysergic acid cyclopentylamide Methylergometrine (Methylergonovine, Methylergobasine) MIPLA MLD-41 PARGY-LAD PRO-LAD
Clavines	9-Deacetoxyfumigaclavine C Agroclavine Chanoclavine Chanoclavine II Costaclavin Cycloclavine Elymoclavine Epoxyagroclavine Festuclavine Fumigaclavine A Fumigaclavine B Fumigaclavine C Paliclavine Penniclavine Setoclavine
Other ergolines	Acetergamine Brazergoline Cianergoline CY-208,243 Delergotrile Disulergine Dosergoside Ergoline Etisulergine Lergotrile Nicergoline Pergolide Proterguride Romergoline Terguride Tiomergine Voxergolide
Related compounds	Adrogolide Naxagolide Quinagolide
Natural sources	Achnatherum robustum (Sleepy Grass) Claviceps spp. (Ergot) Morning glory: Argyreia nervosa (Hawaiian Baby Woodrose), Ipomoea spp.(Morning Glory, Tlitliltzin, Badoh Negro), Rivea corymbosa (Coaxihuitl, Ololiúqui)

Clinical data

Other names	beta-Dihydroergocryptine
Pregnancy category	Contraindicated
Routes of administration	Oral
ATC code	N04BC03 (WHO) (alpha/beta)
Legal status
Legal status	In general: ℞ (Prescription only)
Identifiers
IUPAC name (2R,4R,7R)-N- [(1S,2S,4R,7S)- 2-hydroxy- 7-(S)-(1-methylpropyl)- 5,8-dioxo- 4-(propan-2-yl)- 3-oxa- 6,9-diazatricyclo [7.3.0.0^2,6]dodecan-4-yl]- 6-methyl- 6,11-diazatetracyclo [7.6.1.0^2,7.0^12,16] hexadeca- 1(16),9,12,14-tetraene- 4-carboxamide
CAS Number	88660-47-3
PubChem CID	3084313
ChemSpider	2341400
UNII	5M64643B5U
ChEBI	CHEBI:59925
ChEMBL	ChEMBL1378681
CompTox Dashboard (EPA)	DTXSID90941216
ECHA InfoCard	100.039.157
Chemical and physical data
Formula	C₃₂H₄₃N₅O₅
Molar mass	577.726 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES CCC(C)[C@H]1C(=O)N2CCC[C@H]2[C@]3(N1C(=O)[C@](O3)(C(C)C)NC(=O)[C@@H]4C[C@H]5[C@@H](CC6=CNC7=CC=CC5=C67)N(C4)C)O
InChI InChI=1S/C32H43N5O5/c1-6-18(4)27-29(39)36-12-8-11-25(36)32(41)37(27)30(40)31(42-32,17(2)3)34-28(38)20-13-22-21-9-7-10-23-26(21)19(15-33-23)14-24(22)35(5)16-20/h7,9-10,15,17-18,20,22,24-25,27,33,41H,6,8,11-14,16H2,1-5H3,(H,34,38)/t18?,20-,22-,24-,25+,27+,31-,32+/m1/s1 Key:SBFXHXZNBNFPHV-CROXOCCCSA-N

Epicriptine

References

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